Ethylvanillin → HCID 68633378, compound

HRID 1159414Notes

Reaction equation

HRID 1159414 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.[CH2:20]([O:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][C:30]=1[OH:31])[CH:26]=O)[CH3:21].[OH-].[Na+]>C(Cl)Cl.O>[CH2:20]([O:22][C:23]1[CH:24]=[C:25]([CH2:26][N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:28]=[CH:29][C:30]=1[OH:31])[CH3:21]

Participants

7

Reactant 4

HCID 8467EthylvanillinHCID 14798Sodium HydroxideHCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 68633378HCID 68633378, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

NaB(OAc)3H (8 g, 0.038 mol) was added in portions for 30 min to a mixture of pyrrolidine (3.1 mL, 0.038 mol) and 3-ethoxy-4-hydroxybenzaldehyde (5 g, 0.03 mol) in CH2Cl2 (50 mL) under vigorous stirring and cooling with an ice bath in an atmosphere of argon Ar. The mixture was stirred for 12 h and cooled with an ice bath. 10N NaOH (3.8 mL) and water (30 mL) were added. The organic layer was separated. The aqueous one was extracted with chloroform (2×100 mL). The extracts were evaporated. The residue was purified by chromatography (silica gel 40-63μ, 100 g, CCl4—CHCl3, CHCl3/MeOH 100:0→90:10) to give the title compound (4.8 g, 73%) was obtained as dark-yellow crystals. 1H NMR data (DMSO-d6): 8.65 (s, 1H ArOH), 6.81 (d, 1H, J=1.71, Ar—H), 6.70 (d, 1H, J=7.8, Ar—H); 6.65 (dd, 1H, J1=7.8, J2=1.7, Ar—H), 3.98 (q, 2H, CH2CH3), 3.42 (s, 2H, ArCH2), 2.33-2.45 (m, 4H, pyrrolidine (CH2)2N), 1.59-1.73 (m, 4H, CH2CH2CH2CH2); 1.31 (t, 3H, J=6.9, CH2CH3).

Workup

  1. temperaturecooling with an ice bath in an atmosphere of argon Ar
  2. stirringThe mixture was stirred for 12 h
  3. temperaturecooled with an ice bath
  4. customThe organic layer was separated
  5. extractionThe aqueous one was extracted with chloroform (2×100 mL)
  6. customThe extracts were evaporated
  7. customThe residue was purified by chromatography (silica gel 40-63μ, 100 g, CCl4—CHCl3, CHCl3/MeOH 100:0→90:10)

Sources & evidence

ORD record
ord-73aceecd884049be8dc6cccb6e3e3893
Source dataset
uspto-grants-2010_10
Patent number
US07812040B2

Reaction notes

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